Nothing Special   »   [go: up one dir, main page]

WO2010132524A1 - 2-azatriphenylene materials for organic light emitting diodes - Google Patents

2-azatriphenylene materials for organic light emitting diodes Download PDF

Info

Publication number
WO2010132524A1
WO2010132524A1 PCT/US2010/034479 US2010034479W WO2010132524A1 WO 2010132524 A1 WO2010132524 A1 WO 2010132524A1 US 2010034479 W US2010034479 W US 2010034479W WO 2010132524 A1 WO2010132524 A1 WO 2010132524A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
aryl
group
heteroaryl
formula
Prior art date
Application number
PCT/US2010/034479
Other languages
French (fr)
Inventor
Bin Ma
Raymond C. Kwong
Original Assignee
Universal Display Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Universal Display Corporation filed Critical Universal Display Corporation
Priority to CN2010800280229A priority Critical patent/CN102482222A/en
Priority to KR1020117029712A priority patent/KR101738534B1/en
Priority to EP10720077.6A priority patent/EP2429997B1/en
Priority to JP2012510966A priority patent/JP5937002B2/en
Priority to KR1020177013084A priority patent/KR101884581B1/en
Publication of WO2010132524A1 publication Critical patent/WO2010132524A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
    • C07D421/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.
  • the present invention relates to novel organic materials that may be advantageously used in organic light emitting devices. More particularly, the present invention relates to novel 2-azatriphenylene containing compounds and devices containing such compounds.
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs organic light emitting devices
  • the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
  • One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
  • One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the structure:
  • organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
  • Small molecule refers to any organic material that is not a polymer, and "small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
  • the core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter.
  • a dendrimer may be a "small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • solution processible means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
  • a ligand may be referred to as "photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material.
  • a ligand may be referred to as "ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
  • a first "Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or "higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • the LUMO energy level of a material is higher than the HOMO energy level of the same material.
  • a "higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower” HOMO or LUMO energy level.
  • a first work function is "greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
  • Novel organic compounds comprise 2- azatriphenylene containing compounds that may be advantageously used in OLEDs.
  • these compounds may be used as a host material, hole blocking material, or ligand for an emissive metal complex.
  • Devices containing a 2-azatriphenylene compounds provided herein may have improved stability and efficiency.
  • Novel compounds are provided, the compounds including the structure:
  • R 1 , R 2 , and R 3 may represent mono, di, tri, or tetra substitutions.
  • R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR 1 , R 2 , and R 3 is an aryl or heteroaryl.
  • R3 is a substitution ortho to the nitrogen.
  • One group of compounds are provided wherein the compound has the formula FORMULA I and the compound is not coordinated to a metal.
  • these compounds may be used as host materials in the emissive layer or as non-emitting materials in various other non-emissive layers in OLEDs.
  • R 1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R 1 is an aryl or heteroaryl.
  • R 2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R 2 is an aryl or heteroaryl.
  • R 3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R3 is an aryl or heteroaryl.
  • each OfR 1 , R 2 , and R3 is an aryl or heteroaryl.
  • Particular compounds having FORMULA I are provided including compounds selected from the group consisting of Compound IG - Compound 7OG.
  • R'3, R 4 , R5, R 6 , R 7 , and Rs may represent mono, di, tri, tetra, or penta substitutions.
  • R'3, R 4 , R5, R 6 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • Specific compounds having FORMULA I are also provided.
  • Each OfR 1 , R 2 , R3, R 4 , R5, R 6 , R7, and Rs is hydrogen, such as compounds selected from the group consisting of Compound 1 - Compound 70.
  • Another group of compounds containing a cyclometallated ligand are provided.
  • the compounds comprise a ligand L having the formula:
  • A is a 5-membered or 6-membered aryl or heteroaryl ring.
  • R A may represent a mono, di, tri, or tetra substitution.
  • R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • the ligand L is coordinated to a metal having an atomic number greater than 40.
  • the metal is Ir.
  • These compounds may be used as emitting materials because the cyclometallated complex of such compounds as ligands is expected to provide emissive properties.
  • these compounds may be used as emitting dopants in the emissive layer of an OLED.
  • These compounds may also be used as non-emitting materials.
  • the compounds may be used in parts of a device where the emissive properties of the compound are not used, such as the hole blocking layer.
  • compounds are provided wherein the ligand L is included in a homoleptic compound. In another aspect, compounds are provided wherein the ligand L is included in a heteroleptic compound. In particular, compounds are provided wherein the compound has the formula (L) n (L ') 3 _ n Ir. n is 1 or 2. In one aspect, preferably n is 1. In another aspect, preferably n is 2. L' is selected from the group consisting of:
  • R'i and R' 2 may represent a mono, di, tri, or tetra substitutions.
  • R'i and R' 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • L has a different structure than L'.
  • Compounds comprising particular ligands are also provided, including compounds having a ligand L selected from the group consisting of Compound 71G - Compound 78G.
  • R 4 and R5 may represent mono, di, tri, tetra, or penta substitutions.
  • R 4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • Specific ligands are also provided, including ligands L selected from the group consisting of Compound 71 - Compound 78 (i.e., R 1 , R 2 , R3, R 4 , and R 5 are each hydrogen).
  • Particular compounds comprising an Ir complex containing a 2-azatriphenylene ligand are also provided, including compounds selected from the group consisting of Compound 79G - Compound 96G.
  • R 4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • Specific compounds comprising an Ir complex containing a 2-azatriphenylene ligand are also provided, including compounds selected from the group consisting of Compound 79 - Compound 96 (i.e., R 1 , R 2 , R3, R 4 , Rs, R'i, and R' 2 are each hydrogen).
  • an organic light emitting device comprising an anode, a cathode, and a first organic layer, disposed between the anode and the cathode.
  • the first organic layer further comprising a compound that includes the structure: FORMULA I, as described above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R 1 , R 2 , R3, and A.
  • R 1 , R 2 , and R 3 may represent mono, di, tri, or tetra substitutions.
  • R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR 1 , R 2 , and R 3 is an aryl or heteroaryl.
  • the device comprises a compound having the formula FORMULA I wherein the compound is not coordinated to a metal.
  • Particular compounds that may be used in such devices include compounds selected from the group consisting of Compound IG - Compound 7OG.
  • R'3, R 4 , R5, Rs, R7, and Rs may represent mono, di, tri, tetra, or penta substitutions.
  • R' 3 , R 4 , R 5 , R 6 , R 7 , and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • Certain devices are provided which contain a compound selected from the group consisting of Compound 1 - Compound 70 (i.e., each OfR 1 , R 2 , R3, R 4 , R5, R 6 , R 7 , and Rs is hydrogen).
  • the first organic layer is an emissive layer and the compound including the structure FORMULA I is a host.
  • the first organic layer may further comprise an emitting dopant.
  • the emitting dopant has the formula:
  • R x and R y may represent mono, di, tri, or tetra substitutions.
  • R x and R y are independently selected from the group consisting of hydrogen, alkyl, and aryl.
  • devices are provided wherein the device comprises a compound comprising a ligand L having the formula:
  • A is a 5-membered or 6-membered aryl or heteroaryl ring.
  • R A may represent a mono, di, tri, or tetra substitution.
  • R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • Particular ligands for use in such devices include ligands L selected from the group consisting of Compound 71G - Compound 78G.
  • R 4 and R5 may represent mono, di, tri, tetra, or penta substitutions.
  • R 4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
  • Certain devices are provided which contain a compound having a ligand L selected from the group consisting of Compound 71 - Compound 78 (i.e., R 1 , R 2 , R3, R 4 , and R5 are each hydrogen).
  • Particular compounds for use in such devices include compounds selected from the group consisting of Compound 79G - Compound 96G.
  • R 4 and R 5 may represent mono, di, tri, tetra, or penta substitutions.
  • R 4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
  • Certain devices are provided which contain a compound selected from the group consisting of Compound 79 - Compound 96 (i.e., R 1 , R 2 , R3, R 4 , R5, R'i, and R' 2 are each hydrogen).
  • the first organic layer is an emissive layer and the compound including the structure FORMULA II is an emitting dopant.
  • the first organic layer further comprises a host material.
  • devices wherein the device comprises a second organic layer that is a non-emissive layer.
  • the compound including the structure FORMULA II is a non-emissive material in the second organic layer.
  • the second organic layer is a hole injection or transport layer and the compound including the structure FORMULA II is a hole injection or transport material.
  • a consumer product comprising a device.
  • the device further comprises an anode, a cathode, and a first organic layer disposed between the anode and the cathode.
  • the first organic layer further comprises a compound including the structure FORMULA I, as described above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R 1 , R 2 , R3, and A.
  • R 1 , R 2 , and R3 may represent mono, di, tri, or tetra substitutions.
  • R 1 , R 2 , and R3 are independently selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, heteroaryl and hydrogen. At least one OfR 1 , R 2 , and R 3 is an aryl or heteroaryl.
  • the device of the consumer product may contain a 2-azatriphenylene compound having FORMULA II.
  • the device of the consumer product may contain a compound comprising a ligand including 2-azatriphenylene coordinated to a metal having an atomic number greater than 40.
  • FIG. 1 shows an organic light emitting device.
  • FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
  • FIG. 3 shows a 2-azatriphenylene compound.
  • FIG. 4 shows a ligand containing 2-azatriphenylene.
  • an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • the anode injects holes and the cathode injects electrons into the organic layer(s).
  • the injected holes and electrons each migrate toward the oppositely charged electrode.
  • an "exciton” which is a localized electron-hole pair having an excited energy state, is formed.
  • Light is emitted when the exciton relaxes via a photoemissive mechanism.
  • the exciton may be localized on an excimer or an exciplex. Non- radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • the initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • FIG. 1 shows an organic light emitting device 100.
  • Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160.
  • Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164.
  • Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US 7,279,704 at cols. 6- 10, which are incorporated by reference.
  • each of these layers are available.
  • a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety.
  • An example of a p-doped hole transport layer is m- MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety.
  • n- doped electron transport layer is BPhen doped with Li at a molar ratio of 1 : 1 , as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • Mg metal
  • ITO overlying transparent, electrically-conductive, sputter- deposited ITO layer.
  • FIG. 2 shows an inverted OLED 200.
  • the device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230.
  • Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200.
  • FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
  • FIGS. 1 and 2 The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non- limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
  • the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
  • Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
  • hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer.
  • an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2. [0051] Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No.
  • OLEDs having a single organic layer may be used.
  • OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety.
  • the OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2.
  • the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • Other suitable deposition methods include spin coating and other solution based processes.
  • Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used.
  • the materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
  • Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfmders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.
  • PDAs personal digital assistants
  • Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C, and more preferably at room temperature (20-25 degrees C).
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • halo halogen, alkyl, cycloalkyl, alkenyl, alkynyl, arylkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in US 7,279,704 at cols. 31-32, which are incorporated herein by reference.
  • Novel compounds are provided, the compounds including 2-azatriphenylene (illustrated in FIG. 3).
  • the compounds include 2-azatriphenylene having an additional aromatic substituent (i.e., aryl or heteroaryl). These compounds may be advantageously used in OLEDs to provide devices having improved stability and efficiency.
  • One group of novel compounds include compounds having the formula of FORMULA I without a coordinated metal. Preferably, these compounds are used as non- emitting compounds such as host materials and/or hole blocking layer materials.
  • Another group of novel compounds are provided which include compounds wherein the 2-azatriphenylene structure is incorporated into a ligand coordinated to a metal (illustrated in FIG. 4). These compounds may be expected to demonstrate phosphorescent emissive properties because of the cyclometallated ligand. Thus, these compounds may be preferably used as emitting materials. In addition, these compounds may also be used as non-emitting materials in layers of a device which do not require the emissive properties of such compounds (e.g., hole blocking layer). Particular 2-azatriphenylene ligands include in a compound are provided.
  • 1-azatriphenylene containing compounds have been reported in the literature (see, JP2007189001). However, the class of compounds provided herein contain novel structures. The synthesis provided is directed to making 1-azatriphenylene compounds rather than a synthetic method for making 2-azatriphenylene compounds. Moreover, the 1- azatriphenylene synthetic methods are not necessarily applicable to making 2-azatriphenylene compounds.
  • the additional aromatic substituent i.e., an aryl or a heteroaryl
  • the compounds provided herein may be particularly desirable.
  • the beneficial properties of the compounds may apply to both emissive and non-emissive compounds.
  • Triphenylene is a polyaromatic hydrocarbon with high triplet energy, yet high ⁇ - conjugation and a relatively small energy difference between the first singlet and first triplet levels. This would indicate that triphenylene has relatively easily accessible HOMO and LUMO levels compared to other aromatic compounds with similar triplet energy (e.g., biphenyl). Triphenylene and its derivatives may be especially good hosts at least because these compounds can accommodate red, green and even blue phosphorescent dopants to give high efficiency without energy quenching. High efficiency and high stability PHOLEDs with triphenylene hosts were demonstrated from previous work (see, US2006/0280965 and PCT/US2008/072499).
  • azatriphenylene has a lower LUMO than triphenylene (i.e., a LUMO more accessible than that of triphenylene) and thus azatriphenylene may improve electron transport in OLED devices.
  • azatriphenylene may offer an improved charge balance that results in improvements in device performance in terms of lifetime, efficiency and low voltage.
  • nitrogen in the 2 position of other host materials e.g., aza-dibenzothiophene
  • nitrogen in the 2 position in azatriphenylene containing compounds i.e., 2-azatriphenylene
  • nitrogen in the 2 position in azatriphenylene containing compounds i.e., 2-azatriphenylene
  • the compounds provided may be particularly advantageous because the 2-azatriphenylene containing compounds may be more easily reduced than previously reported triphenylene compounds and derivatives.
  • Table 1 provides the DFT calculation properties of triphenylene and its derivates.
  • Table 1 contains the LUMO level as calculated for triphenylene, 1 -azatriphenylene, and 2-azatriphenylene.
  • the DFT calculation results shown in Table 1 demonstrate that 2-azatriphenylene has a LUMO of -1.34 eV notably lower than triphenylene and 1 -azatriphenylene which have LUMO levels of -0.93 eV and -1.23 eV, respectively.
  • Novel 2-azatriphenylene containing compounds are provided herein. These compounds provide a new type of materials which may be advantageously used in OLEDs. In particular, these compounds may be used in OLEDs fabricated by both vapor deposition or solution processing methods, thereby giving stable and efficient devices.
  • Novel compounds are provided, the compounds include the structure:
  • R 1 , R 2 , and R3 may represent mono, di, tri, or tetra substitutions, and each OfR 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR 1 , R 2 and R 3 is an aryl or a heteroaryl.
  • R 1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • R 1 is an aryl or heteroaryl.
  • R 2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • R 2 is an aryl or heteroaryl.
  • R 3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • R 3 is an aryl or heteroaryl.
  • each OfR 1 , R 2 , and R3 is an aryl or a heteroaryl.
  • One group of compounds provided include compounds having the formula:
  • FORMULA I The compound is not coordinated to a metal.
  • Such compounds may be further substituted at R 1 , R 2 and R3, as described above. These compounds may be used in a variety of layers, both emissive and non-emissive, within the device structure. Preferably, these compounds may be used as hosts in the emissive layer of an OLED. Such compounds may also be preferably used as non-emitting materials in other non-emissive layers of an OLED (e.g., hole blocking layer).
  • R 3 is a substitution ortho to the nitrogen.
  • R 3 substituent at the carbon next to the nitrogen i.e., ortho to the nitrogen
  • the stability of the compound may be improved.
  • the pyridine ring lacking substituents at the positions ortho to the nitrogen atom may be especially vulnerable to degradation and thus less stable.
  • nitrogen bonds exposed in the absence of a substitution ortho to the nitrogen may be the weak link in possible degradation pathways.
  • a substitution ortho to the nitrogen may provide steric protection to the pyridine ring thereby improving stability of the compound. Therefore, a compound having R3 as an substitution ortho to the nitrogen may improve the stability of the 2-azatriphenylene compound.
  • R' 3 , R 4 , R 5 , R 6 , R 7 , and Rs may represent mono, di, tri, terra, or penta substitutions.
  • R'3, R 4 , R5, R 6 , R 7 , and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • the compounds discussed above are not phosphorescent at room temperature. These compounds may be used as non-emitting materials in a device. Preferably, these compounds may be used as a host in the emissive layer of an OLED. More preferably, these compounds may be used as a host in the emissive layer of a phosphorescent OLED. These compounds may also be used as materials in a variety of other non-emissive layers within the device structure, such as a hole blocking material within a hole blocking layer.
  • 2-azatriphenylene compounds which comprise a cyclometallated ligand. These compounds may be expected to have emissive properties as a result of the coordinated metal. Preferably, these compounds may be used as emitting materials within the emissive layer of OLEDs. These compounds may also be used an non-emitting materials in other layers of a device that do not require the emissive properties of the compounds. In particular, these compounds may be used as materials in a hole injection or transport layer.
  • the compounds comprise a ligand L having the formula:
  • the ligand L contains the 2-azatriphenylene structure, described in FORMULA I, with an aromatic substituent A positioned ortho to the nitrogen atom in the aza ring of the compound.
  • A is a 5-membered or 6-membered aryl or heteroaryl ring.
  • R A may represent a mono, di, tri, or tetra substitution.
  • R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • the ligand L is coordinated to a metal having an atomic number greater than 40.
  • the metal is Ir.
  • homoleptic Ir complexes comprising 2-azatriphenylene are provided.
  • compounds are provided wherein the ligand L is included in a homoleptic compound.
  • heteroleptic Ir complexes are provided.
  • compounds are provided wherein the ligand L is included in a heteroleptic compound.
  • compounds having the formula (L) n (L') 3 _ n Ir are provided, n is 1 or 2. In one aspect, preferably n is 1. In another aspect, preferably n is 2.
  • L' is selected from the group consisting of:
  • R'i and R' 2 may represent mono, di, tri, or tetra substitutions.
  • R'i and R' 2 are selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • L has a different structure than L'.
  • R 4 and R5 may represent mono, di, tri, or tetra substitutions.
  • R 4 and R5 are selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • ligand L is selected from the group consisting of:
  • R 4 , R 5 , R'i, and R' 2 may represent mono, di, tri, tetra, or penta substitutions.
  • R 4 , R 5 , R'i, and R' 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • An organic light emitting device comprises an anode, a cathode, and a first organic emissive layer disposed between the anode and the cathode.
  • the first organic emissive layer comprises a compound including the structure FORMULA I, as discussed above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R 15 R 2 , R 3 , and A.
  • R 1 , R 2 , and R 3 may represent mono, di, tri, or tetra substitution.
  • R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. At least one OfR 1 , R 2 , and R 3 is an aryl or heteroaryl.
  • devices which contain a compound wherein R 1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
  • R 1 is an aryl or a heteroaryl.
  • devices are provided which contain a compound wherein R 2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
  • R 2 is an aryl or a heteroaryl.
  • devices which contain a compound wherein R 3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
  • R 3 is an aryl or a heteroaryl.
  • devices are provided which contain a compound wherein R 1 , R 2 , and R 3 are an aryl or a heteroaryl.
  • Devices are provided wherein the device includes a compound having the formula: FORMULA I.
  • the compound is not coordinated to a metal.
  • R'3, R 4 , R5, R 6 , R7, and Rs may represent mono, di, tri, tetra, or penta substitutions.
  • R'3, R 4 , R5, R 6 , R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl.
  • Certain devices are provided which may contain a compound selected from the group consisting of Compound 1 - Compound 70 (i.e., R 1 , R 2 , R 3 , R 4 , R5, R 6 , R7, and R 8 are hydrogen).
  • R3 is a substitution ortho to the nitrogen.
  • the first organic layer is an emissive layer and the compound including the structure FORMULA I is a host.
  • the first organic layer of such a device may further comprise an emitting dopant.
  • the first organic layer may comprise an emitting dopant having the formula:
  • R x and R y may represent mono, di, tri, or tetra substitutions.
  • R x and R y are independently selected from the group consisting of hydrogen, alkyl, and aryl.
  • the first organic layer is an emissive layer and the compound including the structure FORMULA II is an emitting dopant. Moreover, the first organic layer of such a device may further comprise a host material. [0098] Moreover, devices are also provided wherein the device comprises a second organic layer that is a non-emissive layer and the compound including the structure FORMULA II is a non-emissive material in the second organic layer. Preferably, the second organic layer is a hole injection or transport layer and the compound including the structure FORMULA II is a hole injection or transport material.
  • devices wherein the device includes a compound comprising a ligand L having the formula:
  • A is a 5-membered or 6-membered aryl or heteroaryl ring.
  • R A may represent a mono, di, tri, or tetra substitution.
  • R A is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
  • the ligand L is coordinated to a metal having an atomic number greater than 40.
  • the metal is Ir.
  • ligand L is selected from the group consisting of:
  • R 4 and R5 may represent mono, di, tri, terra, or penta substitutions.
  • R 4 and R5 are independently selected from hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl.
  • Devices containing a compound comprising a ligand selected from the group consisting of Compound 71 - Compound 78 are also provided.
  • Devices containing a compound comprising an Ir complex containing a 2- azatriphenylene ligand are also provided, including devices containing a compound selected from the group consisting of Compound 79G - Compound 96G.
  • Devices containing a specific compound are also provided, including devices containing a compound selected from the group consisting of Compound 79 - Compound 96.
  • a consumer product comprising a device.
  • the device further comprises an anode, a cathode, and a first organic layer disposed between the anode and the cathode.
  • the first organic layer further comprises a compound that includes the structure FORMULA I, as described above. Selections for the substituents described as preferred for compounds having FORMULA I are also preferred for use in a device that includes a compound including the structure FORMULA I. These selections include those described for R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R'i, R'2, and A.
  • R 1 , R 2 , and R3 may represent mono, di, tri, or tetra substitution.
  • R 1 , R 2 , and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. At least one OfR 1 , R 2 , and R 3 is an aryl or heteroaryl.
  • the materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device.
  • emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present.
  • the materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
  • Step 1 Synthesis of 4-(biphenyl-2-yl)-2-methoxypyridine.
  • Step 2 Synthesis of 3-methoxydibenzo[f,h]isoquinoline.
  • 4-(biphenyl-2-yl)-2- methoxypyridine (2.9 g, 10.9 mmol), iodine (281 mg, 1.1 mmol) and toluene were charged into a double-walled quartz photochemical reactor equipped with magnetic stirring, an air bubbler and an ultraviolet lamp. Gentle air was bubbled through the solvent while it was irradiated for 15 h.
  • the reaction mixture was purified by flash chromatography on silica (hexane: ethyl acetate) and sonicated in MeOH to give 3-methoxydibenzo[f,h]isoquinoline (0.5 g, 17%).
  • Step 3 Synthesis of dibenzo[£/ ⁇ ]isoquinolin-3-ol.
  • 3-methoxydibenzo[£/z]iso- quinoline (1.0 g, 3.9 mmol) and pyridine hydrochloride (4.5 g, 39 mmol) were heated at ca. 220° C for 1.5 h.
  • the reaction was cooled and water was added.
  • the resulting solids were filtered, wash with water and dried in vacuum to give dibenzo[£/z]isoquinolin-3-ol (0.91 g, 95%).
  • Step 4 Synthesis of dibenzo[/,/ ⁇ ]isoquinolin-3-yl trifluoromethanesulfonate.
  • Trifluoromethanesulfonic anhydride (5.2 g, 19 mmol) was added to a mixture of dibenzo[£/z]isoquinolin-3-ol (0.91 g, 3.7 mmol), pyridine (1.2 g, 15 mmol) and dichloromethane 100 mL under nitrogen at 0 0 C and stirred overnight at room temperature. The reaction was quenched with saturated NaHCCb . The organic layer was washed with water and dried on Na 2 SO 4 . The residue was purified by flash chromatography on silica (hexane: ethyl acetate) to give (1.1 g, 79%).
  • Step S Synthesis of 4-(3-bromophenyl)dibenzo[6, ⁇ /]thiophene.
  • Step 6 Synthesis of 2-(3-(Dibenzo[Mthiophen-4-yl)phenyl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane.
  • Step 7 Synthesis of 3-(3-(dibenzo [b,d] thiophen-4-yl)phenyl)dibenzo [f,h] iso- quinoline.
  • the mixture of Step 4 product dibenzo[f,h]isoquinolin-3-yl trifluoromethanesulfonate (1.1 g, 2.9 mmol)
  • Step 6 product 2-(3-(dibenzo[b,d]thiophen-4- yl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.5 g, 3.8 mmol), potassium phosphate tribasic monohydrate (2.0 g, 8.8 mmol)
  • 150 mL toluene and 15 mL water was prepared and bubbled with nitrogen for 20 minutes.
  • All example devices were fabricated by high vacuum Torr) thermal evaporation.
  • the anode electrode is approximately 800 A or 1200 A of indium tin oxide (ITO).
  • the cathode consisted of 10 A of LiF followed by 1000 A of Al. All devices are encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box ( ⁇ lppm of H 2 O and O 2 ) immediately after fabrication, and a moisture getter was incorporated inside the package.
  • an invention compound, Compound 1 is the host material and the blocking layer material and El is the emitting dopant.
  • the organic stack of Device Examples 1-4 consisted of sequentially, from the ITO surface, 100 A of El as the hole injecting layer (HIL), 300 A of 4,4'-bis-[N-(l-napthyl)-N-phenylamino]biphenyl ( ⁇ - NPD) as the hole transport layer (HTL), 300 A of Compound 1 doped with 10-15 % of El, an Ir phosphorescent compound, as the emissive layer (EML), no blocking layer (0 A) or 50 A of Compound 1 as the blocking layer (BL) and 450 A or 500 A OfAIq 3 (tris-8- hydroxyquinoline aluminum) as the electron transport layer (ETL).
  • Comparative Examples 1 and 2 were fabricated similarly to the Device Examples except that the CBP is used as the host and HPT was used as the BL material or there was no blocking layer.
  • Comp. Ex. is an abbreviation for Comparative example. Ex. is an abbreviation for example. Cmpd. is an abbreviation for Compound.
  • LE luminous efficiency, which is defined as the luminance divided by the driving current density of the OLED.
  • EQE external quantum efficiency, which is defined as the ratio of measured number of photons to the electrons passed across the junction.
  • PE power efficiency, which is defined as the total luminous flux emitted divided by the total power input.
  • Lo is the initial luminance, which is defined as the initial brightness at a certain current density.
  • RTso% is a measure of lifetime, which is defined as the time required for the initial luminance, Lo, to decay to 80% of its value, at a constant current density of 40 mA/cm 2 at room temperature.
  • Comparative Example 1 and Comparative Example 2 use thicknesses and dopant concentrations that were optimized for combinations of materials used in previous device studies.
  • Device Example 1 and Device Example 2 have the same device structure and concentration of materials as used in Comparative Example 1 and Comparative Example 2, but the novel 2-azatriphenylene compounds provided herein have been substituted in place of CBP as the host material and HPT as the blocking layer material.
  • Compound 1 as a host in green phosphorescent OLEDs gives high device efficiency (LE>40 cd/A at 1000 cd/m 2 ), indicating the azatriphenylenes linked with dibenzothiophenes, have triplet energy high enough for efficient green electrophosphorescence. This is consistent with the experimental results that the triplet energy of Compound 1 (Tl : 476 nm), which is high enough to accommodate a green phosphorescent dopant.
  • Tso% (defined as the time required for the initial luminance, Lo, to decay to 80% of its value, at a constant current density of 40 mA/cm 2 at room temperature) for Device Example 3 and Comparative 1 are 136 hours and 105 hours respectively, with Device Example 1 having a slightly higher Lo.
  • hosts containing azatriphenylenes are good host and enhancement layer materials for phosphorescent OLEDs, providing as least the similar efficiency and improvement in stability compared to the commonly used CBP as the host.
  • More conjugated versions of triphenylene containing benzoselenophenes for example triphenylene and dibenzoselenophene units linked via/?-phenylene (such as 4,4'-biphenyl) may be very suitable for lower energy (yellow to red) phosphorescent OLEDs.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Compounds containing 2-azatriphenylene are provided. In particular, compounds containing a 2-azatriphenylene core having an additional aromatic group are provided. The compounds provided may be emissive or non-emissive materials. The compounds may be used in organic light emitting devices, particularly as host materials, hole blocking layer materials, or emitting dopants. Devices comprising 2-azatriphenylene containing compounds may demonstrate improved stability and efficiency.

Description

2-AZATRIPHENYLENE MATERIALS FOR ORGANIC LIGHT EMITTING DIODES
[0001] This application claims priority to U.S. Provisional Application Serial No. 61/177,435, filed May 12, 2009, the disclosure of which is herein expressly incorporated by reference in its entirety.
[0002] The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.
FIELD OF THE INVENTION
[0003] The present invention relates to novel organic materials that may be advantageously used in organic light emitting devices. More particularly, the present invention relates to novel 2-azatriphenylene containing compounds and devices containing such compounds.
BACKGROUND
[0004] Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
[0005] OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety. [0006] One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these standards call for saturated red, green, and blue pixels. Color may be measured using CIE coordinates, which are well known to the art.
[0007] One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the structure:
Figure imgf000004_0001
[0008] In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.
[0009] As used herein, the term "organic" includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule" class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a "small molecule," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
[0010] As used herein, "top" means furthest away from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as "disposed over" a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode may be described as "disposed over" an anode, even though there are various organic layers in between. [0011] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
[0012] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
[0013] As used herein, and as would be generally understood by one skilled in the art, a first "Highest Occupied Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower" HOMO or LUMO energy level.
[0014] As used herein, and as would be generally understood by one skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a "higher" work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
[0015] More details on OLEDs, and the definitions described above, can be found in US Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.
SUMMARY OF THE INVENTION [0016] Novel organic compounds are provided. The compounds comprise 2- azatriphenylene containing compounds that may be advantageously used in OLEDs. In particular, these compounds may be used as a host material, hole blocking material, or ligand for an emissive metal complex. Devices containing a 2-azatriphenylene compounds provided herein may have improved stability and efficiency. Novel compounds are provided, the compounds including the structure:
Figure imgf000006_0001
FORMULA I.
[0017] R1, R2, and R3 may represent mono, di, tri, or tetra substitutions. R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR1, R2, and R3 is an aryl or heteroaryl. Preferably, R3 is a substitution ortho to the nitrogen.
[0018] One group of compounds are provided wherein the compound has the formula FORMULA I and the compound is not coordinated to a metal. Preferably, these compounds may be used as host materials in the emissive layer or as non-emitting materials in various other non-emissive layers in OLEDs.
[0019] Preferably, R1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R1 is an aryl or heteroaryl. Preferably, R2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R2 is an aryl or heteroaryl. Preferably, R3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. More preferably, R3 is an aryl or heteroaryl. Preferably, each OfR1, R2, and R3 is an aryl or heteroaryl.
[0020] Particular compounds having FORMULA I are provided including compounds selected from the group consisting of Compound IG - Compound 7OG. R'3, R4, R5, R6, R7, and Rs may represent mono, di, tri, tetra, or penta substitutions. R'3, R4, R5, R6 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Specific compounds having FORMULA I are also provided. Each OfR1, R2, R3, R4, R5, R6, R7, and Rs is hydrogen, such as compounds selected from the group consisting of Compound 1 - Compound 70.
[0021] Another group of compounds containing a cyclometallated ligand are provided. The compounds comprise a ligand L having the formula:
Figure imgf000007_0001
FORMULA II.
[0022] A is a 5-membered or 6-membered aryl or heteroaryl ring. RA may represent a mono, di, tri, or tetra substitution. RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. The ligand L is coordinated to a metal having an atomic number greater than 40. Preferably, the metal is Ir.
[0023] These compounds may be used as emitting materials because the cyclometallated complex of such compounds as ligands is expected to provide emissive properties. Preferably, these compounds may be used as emitting dopants in the emissive layer of an OLED. These compounds may also be used as non-emitting materials. In particular, the compounds may be used in parts of a device where the emissive properties of the compound are not used, such as the hole blocking layer.
[0024] In one aspect, compounds are provided wherein the ligand L is included in a homoleptic compound. In another aspect, compounds are provided wherein the ligand L is included in a heteroleptic compound. In particular, compounds are provided wherein the compound has the formula (L)n(L ')3_nIr. n is 1 or 2. In one aspect, preferably n is 1. In another aspect, preferably n is 2. L' is selected from the group consisting of:
Figure imgf000008_0001
R'i and R'2 may represent a mono, di, tri, or tetra substitutions. R'i and R'2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. L has a different structure than L'.
[0025] Compounds comprising particular ligands are also provided, including compounds having a ligand L selected from the group consisting of Compound 71G - Compound 78G. R4 and R5 may represent mono, di, tri, tetra, or penta substitutions. R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Specific ligands are also provided, including ligands L selected from the group consisting of Compound 71 - Compound 78 (i.e., R1, R2, R3, R4, and R5 are each hydrogen).
[0026] Particular compounds comprising an Ir complex containing a 2-azatriphenylene ligand are also provided, including compounds selected from the group consisting of Compound 79G - Compound 96G. R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Specific compounds comprising an Ir complex containing a 2-azatriphenylene ligand are also provided, including compounds selected from the group consisting of Compound 79 - Compound 96 (i.e., R1, R2, R3, R4, Rs, R'i, and R'2 are each hydrogen).
[0027] Additionally, an organic light emitting device is also provided. The device comprising an anode, a cathode, and a first organic layer, disposed between the anode and the cathode. The first organic layer further comprising a compound that includes the structure:
Figure imgf000009_0001
FORMULA I, as described above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R1, R2, R3, and A.
[0028] R1, R2, and R3 may represent mono, di, tri, or tetra substitutions. R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR1, R2, and R3 is an aryl or heteroaryl.
[0029] In one aspect, the device comprises a compound having the formula FORMULA I wherein the compound is not coordinated to a metal. Particular compounds that may be used in such devices include compounds selected from the group consisting of Compound IG - Compound 7OG. R'3, R4, R5, Rs, R7, and Rs may represent mono, di, tri, tetra, or penta substitutions. R'3, R4, R5, R6, R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Certain devices are provided which contain a compound selected from the group consisting of Compound 1 - Compound 70 (i.e., each OfR1, R2, R3, R4, R5, R6, R7, and Rs is hydrogen).
[0030] In another aspect, devices are provided wherein the first organic layer is an emissive layer and the compound including the structure FORMULA I is a host. Moreover, the first organic layer may further comprise an emitting dopant. Preferably, the emitting dopant has the formula:
Figure imgf000009_0002
E1 . Rx and Ry may represent mono, di, tri, or tetra substitutions. Rx and Ry are independently selected from the group consisting of hydrogen, alkyl, and aryl. [0031] Additionally, devices are provided wherein the device comprises a compound comprising a ligand L having the formula:
Figure imgf000010_0001
FORMULA II.
[0032] A is a 5-membered or 6-membered aryl or heteroaryl ring. RA may represent a mono, di, tri, or tetra substitution. RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
[0033] Particular ligands for use in such devices include ligands L selected from the group consisting of Compound 71G - Compound 78G. R4 and R5 may represent mono, di, tri, tetra, or penta substitutions. R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. Certain devices are provided which contain a compound having a ligand L selected from the group consisting of Compound 71 - Compound 78 (i.e., R1, R2, R3, R4, and R5 are each hydrogen).
[0034] Particular compounds for use in such devices include compounds selected from the group consisting of Compound 79G - Compound 96G. R4 and R5 may represent mono, di, tri, tetra, or penta substitutions. R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. Certain devices are provided which contain a compound selected from the group consisting of Compound 79 - Compound 96 (i.e., R1, R2, R3, R4, R5, R'i, and R'2 are each hydrogen).
[0035] In one aspect, devices are provided wherein the first organic layer is an emissive layer and the compound including the structure FORMULA II is an emitting dopant. Preferably, the first organic layer further comprises a host material.
[0036] In another aspect, devices are provided wherein the device comprises a second organic layer that is a non-emissive layer. The compound including the structure FORMULA II is a non-emissive material in the second organic layer. Preferably, the second organic layer is a hole injection or transport layer and the compound including the structure FORMULA II is a hole injection or transport material.
[0037] Additionally, a consumer product comprising a device is also provided. The device further comprises an anode, a cathode, and a first organic layer disposed between the anode and the cathode. The first organic layer further comprises a compound including the structure FORMULA I, as described above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R1, R2, R3, and A.
[0038] R1, R2, and R3 may represent mono, di, tri, or tetra substitutions. R1, R2, and R3 are independently selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, heteroaryl and hydrogen. At least one OfR1, R2, and R3 is an aryl or heteroaryl.
[0039] In one aspect, the device of the consumer product may contain a 2-azatriphenylene compound having FORMULA II. In another aspect, the device of the consumer product may contain a compound comprising a ligand including 2-azatriphenylene coordinated to a metal having an atomic number greater than 40.
BRIEF DESCRIPTION OF THE DRAWINGS [0040] FIG. 1 shows an organic light emitting device.
[0041] FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
[0042] FIG. 3 shows a 2-azatriphenylene compound.
[0043] FIG. 4 shows a ligand containing 2-azatriphenylene.
DETAILED DESCRIPTION
[0044] Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an "exciton," which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non- radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
[0045] The initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
[0046] More recently, OLEDs having emissive materials that emit light from triplet states ("phosphorescence") have been demonstrated. Baldo et al, "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, vol. 395, 151-154, 1998; ("Baldo-I") and Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) ("Baldo-II"), which are incorporated by reference in their entireties. Phosphorescence is described in more detail in US Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.
[0047] FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US 7,279,704 at cols. 6- 10, which are incorporated by reference.
[0048] More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m- MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n- doped electron transport layer is BPhen doped with Li at a molar ratio of 1 : 1 , as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg: Ag with an overlying transparent, electrically-conductive, sputter- deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.
[0049] FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
[0050] The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non- limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2. [0051] Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
[0052] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing. [0053] Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfmders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C, and more preferably at room temperature (20-25 degrees C).
[0054] The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.
[0055] The terms halo, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, arylkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in US 7,279,704 at cols. 31-32, which are incorporated herein by reference.
[0056] Novel compounds are provided, the compounds including 2-azatriphenylene (illustrated in FIG. 3). In particular, the compounds include 2-azatriphenylene having an additional aromatic substituent (i.e., aryl or heteroaryl). These compounds may be advantageously used in OLEDs to provide devices having improved stability and efficiency.
[0057] One group of novel compounds include compounds having the formula of FORMULA I without a coordinated metal. Preferably, these compounds are used as non- emitting compounds such as host materials and/or hole blocking layer materials.
[0058] Another group of novel compounds are provided which include compounds wherein the 2-azatriphenylene structure is incorporated into a ligand coordinated to a metal (illustrated in FIG. 4). These compounds may be expected to demonstrate phosphorescent emissive properties because of the cyclometallated ligand. Thus, these compounds may be preferably used as emitting materials. In addition, these compounds may also be used as non-emitting materials in layers of a device which do not require the emissive properties of such compounds (e.g., hole blocking layer). Particular 2-azatriphenylene ligands include in a compound are provided.
[0059] 1-azatriphenylene containing compounds have been reported in the literature (see, JP2007189001). However, the class of compounds provided herein contain novel structures. The synthesis provided is directed to making 1-azatriphenylene compounds rather than a synthetic method for making 2-azatriphenylene compounds. Moreover, the 1- azatriphenylene synthetic methods are not necessarily applicable to making 2-azatriphenylene compounds.
[0060] The methods provided herein are directed to 2-azatriphenylene compounds.
[0061] At least one example of 2-azatriphenylene compounds is reported in the literature (see, Hewline, M. et al., Synthesis, 14: 2157-2163, 2007). However, the reference does not provide compounds having the additional aromatic substituent as provided herein and does not suggest 2-azatriphenylene compounds in the context of an OLED. 2-azatriphenylene compounds lacking the additional aromatic substituent may not be suitable for use in OLEDs. The additional aromatic group substituent at R1, R2, and/or R3 on the 2-azatriphenylene core of the compound provides a novel structure and may also provide beneficial properties. In particular, the additional aromatic substituent (i.e., an aryl or a heteroaryl) may provide a further improvement in the stability of the compound via the additional conjugation. In addition, there are no known references providing synthetic methods for making 2- azatriphenylene compounds. Thus, for at least these reasons, the compounds provided herein may be particularly desirable. The beneficial properties of the compounds may apply to both emissive and non-emissive compounds.
[0062] Moreover, most of the azatriphenylene compounds previously reported are 1- azatriphenylene compounds. While the synthesis of 1-azatriphenylenes is believed to be well known, the synthetic methods for making 1-azatriphenylenes do not necessarily apply to making 2-azatriphenylene compounds. Despite previous reports of azatriphenylene compounds, there have been no reports regarding the synthetic methods for making such 2- azatriphenylene compounds as provided herein. Many of the novel 2-azatriphenylene compounds provided can be synthesized using the methods described herein.
[0063] Triphenylene is a polyaromatic hydrocarbon with high triplet energy, yet high π- conjugation and a relatively small energy difference between the first singlet and first triplet levels. This would indicate that triphenylene has relatively easily accessible HOMO and LUMO levels compared to other aromatic compounds with similar triplet energy (e.g., biphenyl). Triphenylene and its derivatives may be especially good hosts at least because these compounds can accommodate red, green and even blue phosphorescent dopants to give high efficiency without energy quenching. High efficiency and high stability PHOLEDs with triphenylene hosts were demonstrated from previous work (see, US2006/0280965 and PCT/US2008/072499).
[0064] Compounds containing the triphenylene derivative azatriphenylene may be especially beneficial. Azatriphenylene has a lower LUMO than triphenylene (i.e., a LUMO more accessible than that of triphenylene) and thus azatriphenylene may improve electron transport in OLED devices. In addition, azatriphenylene may offer an improved charge balance that results in improvements in device performance in terms of lifetime, efficiency and low voltage. Moreover, previous work has shown that nitrogen in the 2 position of other host materials (e.g., aza-dibenzothiophene) may provide improvements. Without being limited to any theory as to how the invention works, it is thought that nitrogen in the 2 position in azatriphenylene containing compounds (i.e., 2-azatriphenylene) may also provide beneficial properties.
[0065] In addition, the compounds provided may be particularly advantageous because the 2-azatriphenylene containing compounds may be more easily reduced than previously reported triphenylene compounds and derivatives. Table 1 provides the DFT calculation properties of triphenylene and its derivates. In particular, Table 1 contains the LUMO level as calculated for triphenylene, 1 -azatriphenylene, and 2-azatriphenylene. The DFT calculation results shown in Table 1 demonstrate that 2-azatriphenylene has a LUMO of -1.34 eV notably lower than triphenylene and 1 -azatriphenylene which have LUMO levels of -0.93 eV and -1.23 eV, respectively. Additionally, the DFT calculations shown in Table 1 suggest that the triplet energy of 2-azatriphenylene is similar to the triplet energy of triphenylene and 1 -azatriphenylene, which was confirmed by the experimental results of Compound 1. Therefore, 2-azatriphenylene containing compounds may be more easily reduced and thus provide devices with low operating voltage.
TABLE 1
Figure imgf000017_0001
Figure imgf000018_0002
[0066] Novel 2-azatriphenylene containing compounds are provided herein. These compounds provide a new type of materials which may be advantageously used in OLEDs. In particular, these compounds may be used in OLEDs fabricated by both vapor deposition or solution processing methods, thereby giving stable and efficient devices.
[0067] Novel compounds are provided, the compounds include the structure:
Figure imgf000018_0001
FORMULA I.
[0068] R1, R2, and R3 may represent mono, di, tri, or tetra substitutions, and each OfR1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. At least one OfR1, R2 and R3 is an aryl or a heteroaryl.
[0069] In one aspect, R1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Preferably, R1 is an aryl or heteroaryl. In another aspect, R2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Preferably, R2 is an aryl or heteroaryl. In yet another aspect, R3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. Preferably, R3 is an aryl or heteroaryl. In a further aspect, each OfR1, R2, and R3 is an aryl or a heteroaryl.
[0070] One group of compounds provided include compounds having the formula:
Figure imgf000019_0001
FORMULA I. The compound is not coordinated to a metal.
[0071] Such compounds may be further substituted at R1, R2 and R3, as described above. These compounds may be used in a variety of layers, both emissive and non-emissive, within the device structure. Preferably, these compounds may be used as hosts in the emissive layer of an OLED. Such compounds may also be preferably used as non-emitting materials in other non-emissive layers of an OLED (e.g., hole blocking layer).
[0072] Preferably, R3 is a substitution ortho to the nitrogen. By adding the R3 substituent at the carbon next to the nitrogen (i.e., ortho to the nitrogen), the stability of the compound may be improved. Without being bound by theory, it is thought that that the pyridine ring lacking substituents at the positions ortho to the nitrogen atom may be especially vulnerable to degradation and thus less stable. In particular, without being bound by theory, it is believed that nitrogen bonds exposed in the absence of a substitution ortho to the nitrogen may be the weak link in possible degradation pathways. Thus, a substitution ortho to the nitrogen may provide steric protection to the pyridine ring thereby improving stability of the compound. Therefore, a compound having R3 as an substitution ortho to the nitrogen may improve the stability of the 2-azatriphenylene compound.
[0073] Particular compounds having the formula of FORMULA I are provided, wherein the compound is selected from the group consisting of:
Figure imgf000020_0001
Figure imgf000021_0001
Compound 9G
Figure imgf000021_0003
Figure imgf000021_0002
Compound 11 G Compound 12G
Figure imgf000021_0004
Compound 13G Compound 14G
Figure imgf000021_0005
Compound 15G Compound 16G
Figure imgf000022_0001
Compound 17G Compound 18G
Figure imgf000022_0002
Compound 19G Compound 2OG
Figure imgf000022_0003
Compound 24G
Compound 23G
Figure imgf000023_0001
Compound 31 G
Figure imgf000024_0001
Compound 36G
Figure imgf000024_0002
Figure imgf000024_0004
Figure imgf000024_0003
Compound 4OG
Figure imgf000025_0001
Figure imgf000025_0002
Compound 44G
Figure imgf000025_0003
Figure imgf000025_0004
Compound 45G
Figure imgf000025_0006
Compound 47G
Figure imgf000025_0005
Compound 48G
Figure imgf000026_0001
Compound 49G
Figure imgf000026_0003
Compound 51 G
Figure imgf000026_0002
Compound 52G
Figure imgf000026_0004
Compound 56G
Compound 55G
Figure imgf000027_0001
Compound 57G
Figure imgf000027_0002
Figure imgf000027_0003
Compound 6OG
Compound 59G
Figure imgf000027_0004
Compound 64G
Compound 63G
Figure imgf000028_0001
Compound 66G
Figure imgf000028_0002
Compound 67G R4 Compound 68G
Figure imgf000028_0003
Compound 69G
[0074] R'3, R4, R5, R6, R7, and Rs may represent mono, di, tri, terra, or penta substitutions. R'3, R4, R5, R6, R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
[0075] In addition, specific examples of compounds having the formula of FORMULA I also are provided. Each of the substituents R1, R2, R3, R'3, R4, R5, R6, R7, and Rs is hydrogen. Specific compounds provided include compounds selected from the group consisting of:
Figure imgf000029_0001
Figure imgf000029_0002
Compound 3
Figure imgf000029_0003
Figure imgf000029_0004
Compound 5
Figure imgf000029_0006
Figure imgf000029_0005
Figure imgf000030_0001
Compound 9
Figure imgf000030_0002
Compound 11
Figure imgf000030_0003
Compound 14
Figure imgf000030_0004
Figure imgf000030_0005
Figure imgf000031_0001
Compound 20
Compound 19
Figure imgf000031_0002
Compound 21
Figure imgf000031_0003
Figure imgf000031_0004
Figure imgf000032_0001
Compound 28
Compound 27
Figure imgf000032_0002
Compound 29
Figure imgf000032_0003
Figure imgf000032_0004
Compound 32
Compound 31
Figure imgf000032_0005
Compound 33
Figure imgf000032_0006
Figure imgf000033_0001
Compound 35
Figure imgf000033_0002
Figure imgf000033_0004
Compound 39
Figure imgf000033_0003
Compound 40
Figure imgf000033_0005
Figure imgf000034_0001
Compound 44
Figure imgf000034_0002
Figure imgf000034_0003
Compound 45
Figure imgf000034_0005
Compound 47
Figure imgf000034_0004
Compound 48
Figure imgf000034_0006
Compound 49
Figure imgf000034_0007
Compound 50
Figure imgf000035_0001
Compound 51
Figure imgf000035_0003
Figure imgf000035_0002
Figure imgf000035_0004
Compound 56
Compound 55
Figure imgf000035_0005
Compound 57
Figure imgf000035_0006
Figure imgf000036_0001
Figure imgf000036_0002
Compound 60
Compound 59
Figure imgf000036_0003
Compound 64
Compound 63
Figure imgf000036_0004
Figure imgf000037_0002
Figure imgf000037_0001
Compound 70
Compound 69
[0076] The compounds discussed above (i.e, having the formula of FORMULA I without a coordinated metal) are not phosphorescent at room temperature. These compounds may be used as non-emitting materials in a device. Preferably, these compounds may be used as a host in the emissive layer of an OLED. More preferably, these compounds may be used as a host in the emissive layer of a phosphorescent OLED. These compounds may also be used as materials in a variety of other non-emissive layers within the device structure, such as a hole blocking material within a hole blocking layer.
[0077] Another group of novel compounds provided herein are 2-azatriphenylene compounds which comprise a cyclometallated ligand. These compounds may be expected to have emissive properties as a result of the coordinated metal. Preferably, these compounds may be used as emitting materials within the emissive layer of OLEDs. These compounds may also be used an non-emitting materials in other layers of a device that do not require the emissive properties of the compounds. In particular, these compounds may be used as materials in a hole injection or transport layer.
[0078] The compounds comprise a ligand L having the formula:
Figure imgf000038_0001
FORMULA II.
[0079] The ligand L contains the 2-azatriphenylene structure, described in FORMULA I, with an aromatic substituent A positioned ortho to the nitrogen atom in the aza ring of the compound.
[0080] A is a 5-membered or 6-membered aryl or heteroaryl ring. RA may represent a mono, di, tri, or tetra substitution. RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. The ligand L is coordinated to a metal having an atomic number greater than 40. Preferably, the metal is Ir.
[0081] In one aspect, homoleptic Ir complexes comprising 2-azatriphenylene are provided. In particular, compounds are provided wherein the ligand L is included in a homoleptic compound. In another aspect, heteroleptic Ir complexes are provided. In particular, compounds are provided wherein the ligand L is included in a heteroleptic compound. In yet another aspect, compounds having the formula (L)n(L')3_nIr are provided, n is 1 or 2. In one aspect, preferably n is 1. In another aspect, preferably n is 2. L' is selected from the group consisting of:
Figure imgf000038_0002
[0082] R'i and R'2 may represent mono, di, tri, or tetra substitutions. R'i and R'2 are selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. [0083] L has a different structure than L'.
[0084] Compounds including particular 2-azatriphenylene ligands are provided. The compound containing a ligand L selected from the group consisting of:
Figure imgf000039_0001
Compound 73G
Figure imgf000039_0002
Compound 74G Compound 75G
Figure imgf000039_0003
Figure imgf000039_0004
Compound 76G
Figure imgf000039_0005
Compound 78G [0085] R4 and R5 may represent mono, di, tri, or tetra substitutions. R4 and R5 are selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
[0086] In addition, compounds containing a specific 2-azatriphenylene ligand are provided. The ligand L is selected from the group consisting of:
Figure imgf000040_0001
Compound 71 Compound 72 Compound 73
Figure imgf000040_0002
Compound 74 Compound 75 Compound 75'
Figure imgf000040_0003
Compound 76 Compound 77 Compound 78 [0087] Particular compounds comprising an Ir complex containing a 2-azatriphenylene ligand are provided, including compounds selected from the group consisting of:
Figure imgf000041_0001
Compound 80 Compound 81
Figure imgf000041_0002
Compound 83
Figure imgf000041_0003
Figure imgf000041_0005
Figure imgf000041_0004
Compound 85 Compound 86 Compound 87
Figure imgf000042_0001
Compound 90 Compound 91 Compound 92
Figure imgf000042_0002
Figure imgf000042_0003
Compound 94
Figure imgf000043_0001
Compound 95 Compound 96
[0088] R4, R5, R'i, and R'2 may represent mono, di, tri, tetra, or penta substitutions. R4, R5, R'i, and R' 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
[0089] In addition, specific iridium complexes containing 2-azatriphenylene are also provided, including compounds selected from the group consisting of:
Figure imgf000043_0002
Compound 79 Compound 80 Compound 81
Figure imgf000043_0003
Compound 82 Compound 83 Compound 84
Figure imgf000044_0001
Compound 85 Compound 86 Compound 87
Figure imgf000044_0002
Compound 88 Compound 89 Compound 90
Figure imgf000044_0003
Compound 91 Compound 92 Compound 93
Figure imgf000045_0001
Compound 94 Compound 95 Compound 96
[0090] An organic light emitting device is also provided. The device comprises an anode, a cathode, and a first organic emissive layer disposed between the anode and the cathode. The first organic emissive layer comprises a compound including the structure FORMULA I, as discussed above. Selections for the substituents described as preferred for the compounds including the structure FORMULA I are also preferred for use in a device that comprises a compound including the structure FORMULA I. These selections include those described for R15 R2, R3, and A.
[0091] R1, R2, and R3 may represent mono, di, tri, or tetra substitution. R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. At least one OfR1, R2, and R3 is an aryl or heteroaryl.
[0092] In one aspect, devices are provided which contain a compound wherein R1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. Preferably, R1 is an aryl or a heteroaryl. In another aspect, devices are provided which contain a compound wherein R2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. Preferably, R2 is an aryl or a heteroaryl. In yet another aspect, devices are provided which contain a compound wherein R3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. Preferably, R3 is an aryl or a heteroaryl. In a further aspect, devices are provided which contain a compound wherein R1, R2, and R3 are an aryl or a heteroaryl.
[0093] Devices are provided wherein the device includes a compound having the formula:
Figure imgf000046_0001
FORMULA I. The compound is not coordinated to a metal.
[0094] Particular devices are provided, the device comprising a compound selected from the group consisting of Compound IG - Compound 7OG. R'3, R4, R5, R6, R7, and Rs may represent mono, di, tri, tetra, or penta substitutions. R'3, R4, R5, R6, R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl. Certain devices are provided which may contain a compound selected from the group consisting of Compound 1 - Compound 70 (i.e., R1, R2, R3, R4, R5, R6, R7, and R8 are hydrogen).
[0095] Preferably, R3 is a substitution ortho to the nitrogen.
[0096] Additionally, devices are provided wherein the first organic layer is an emissive layer and the compound including the structure FORMULA I is a host. Moreover, the first organic layer of such a device may further comprise an emitting dopant. In particular, the first organic layer may comprise an emitting dopant having the formula:
Figure imgf000046_0002
E1
Rx and Ry may represent mono, di, tri, or tetra substitutions. Rx and Ry are independently selected from the group consisting of hydrogen, alkyl, and aryl.
[0097] Additionally, devices are also provided wherein the first organic layer is an emissive layer and the compound including the structure FORMULA II is an emitting dopant. Moreover, the first organic layer of such a device may further comprise a host material. [0098] Moreover, devices are also provided wherein the device comprises a second organic layer that is a non-emissive layer and the compound including the structure FORMULA II is a non-emissive material in the second organic layer. Preferably, the second organic layer is a hole injection or transport layer and the compound including the structure FORMULA II is a hole injection or transport material.
[0099] In another aspect, devices are provided wherein the device includes a compound comprising a ligand L having the formula:
Figure imgf000047_0001
FORMULA II.
[0100] A is a 5-membered or 6-membered aryl or heteroaryl ring. RA may represent a mono, di, tri, or tetra substitution. RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl. The ligand L is coordinated to a metal having an atomic number greater than 40. Preferably, the metal is Ir.
[0101] Particular devices are provided wherein the ligand L is selected from the group consisting of:
Figure imgf000047_0002
Figure imgf000047_0003
Compound 72G Compound 73G
Figure imgf000048_0001
Compound 74G Compound 75G
Figure imgf000048_0002
Figure imgf000048_0003
Compound 76G
Figure imgf000048_0004
Compound 78G
[0102] R4 and R5 may represent mono, di, tri, terra, or penta substitutions. R4 and R5 are independently selected from hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl.
[0103] Devices containing a compound comprising a ligand selected from the group consisting of Compound 71 - Compound 78 are also provided.
[0104] Devices containing a compound comprising an Ir complex containing a 2- azatriphenylene ligand are also provided, including devices containing a compound selected from the group consisting of Compound 79G - Compound 96G. Devices containing a specific compound are also provided, including devices containing a compound selected from the group consisting of Compound 79 - Compound 96.
[0105] Additionally, a consumer product comprising a device is also provided. The device further comprises an anode, a cathode, and a first organic layer disposed between the anode and the cathode. The first organic layer further comprises a compound that includes the structure FORMULA I, as described above. Selections for the substituents described as preferred for compounds having FORMULA I are also preferred for use in a device that includes a compound including the structure FORMULA I. These selections include those described for R1, R2, R3, R4, R5, R6, R7, R8, R'i, R'2, and A.
[0106] R1, R2, and R3 may represent mono, di, tri, or tetra substitution. R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl. At least one OfR1, R2, and R3 is an aryl or heteroaryl.
[0107] The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
[0108] In addition to and / or in combination with the materials disclosed herein, many hole injection materials, hole transporting materials, host materials, dopant materials, exiton/hole blocking layer materials, electron transporting and electron injecting materials may be used in an OLED. Non-limiting examples of the materials that may be used in an OLED in combination with materials disclosed herein are listed in Table 2 below. Table 2 lists non- limiting classes of materials, non- limiting examples of compounds for each class, and references that disclose the materials.
TABLE 2
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0003
EXPERIMENTAL
Compound Examples
Example 1. Synthesis of Compound 1
Figure imgf000061_0001
[0109] Step 1. Synthesis of 4-(biphenyl-2-yl)-2-methoxypyridine. A nitrogen flushed mixture of 4-chloro-2-methoxypyridine (3.0 g, 21.03 mmol), 2-biphenylboronic acid 5.0 g, 25.23 mmol), Pd2(dba)3 (381 mg, 0.414 mmol), 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl (681 mg, 1.66 mmol), toluene (250 mL) and a slurry OfK3PO4H2O (14.57 g, 63.09 mmol) in water (25 mL) were refluxed for 18 h. After the mixture cooled to room temperature the organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by flash chromatography on silica (hexane: ethyl acetate) and recrystallized from ethyl acetate to give 4-(biphenyl-2-yl)-2- methoxypyridine (4.2 g, 76.5%).
Figure imgf000061_0002
[0110] Step 2. Synthesis of 3-methoxydibenzo[f,h]isoquinoline. 4-(biphenyl-2-yl)-2- methoxypyridine (2.9 g, 10.9 mmol), iodine (281 mg, 1.1 mmol) and toluene were charged into a double-walled quartz photochemical reactor equipped with magnetic stirring, an air bubbler and an ultraviolet lamp. Gentle air was bubbled through the solvent while it was irradiated for 15 h. The reaction mixture was purified by flash chromatography on silica (hexane: ethyl acetate) and sonicated in MeOH to give 3-methoxydibenzo[f,h]isoquinoline (0.5 g, 17%).
Figure imgf000062_0001
[0111] Step 3. Synthesis of dibenzo[£/ι]isoquinolin-3-ol. 3-methoxydibenzo[£/z]iso- quinoline (1.0 g, 3.9 mmol) and pyridine hydrochloride (4.5 g, 39 mmol) were heated at ca. 220° C for 1.5 h. The reaction was cooled and water was added. The resulting solids were filtered, wash with water and dried in vacuum to give dibenzo[£/z]isoquinolin-3-ol (0.91 g, 95%).
Figure imgf000062_0002
[0112] Step 4. Synthesis of dibenzo[/,/ι]isoquinolin-3-yl trifluoromethanesulfonate.
Trifluoromethanesulfonic anhydride (5.2 g, 19 mmol) was added to a mixture of dibenzo[£/z]isoquinolin-3-ol (0.91 g, 3.7 mmol), pyridine (1.2 g, 15 mmol) and dichloromethane 100 mL under nitrogen at 0 0C and stirred overnight at room temperature. The reaction was quenched with saturated NaHCCb . The organic layer was washed with water and dried on Na2SO4. The residue was purified by flash chromatography on silica (hexane: ethyl acetate) to give (1.1 g, 79%).
Figure imgf000062_0003
[0113] Step S. Synthesis of 4-(3-bromophenyl)dibenzo[6,</]thiophene. A nitrogen flushed mixture of 1, 3-dibromobenzene (18.63 g, 78.92 mmol), dibenzo{b,d}thiophen-4- ylboronic acid (6.0 g, 26.3 mmol), Pd(PPh3)4 (304 mg, 0.414 mmol), toluene (200 mL) and a slurry of K2CO3 (10.9 g, 78.92 mmol) in water (20 mL) were refluxed for 23 h. After the mixture cooled to room temperature the organic layer was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by vacuum distillation (Kugelrohr) followed by flash chromatography on silica (hexane: dichloromethane) to give 4-(3-bromophenyl)dibenzo[δ,J]thiophene (3.5 g 39.2 %).
Figure imgf000063_0001
[0114] Step 6. Synthesis of 2-(3-(Dibenzo[Mthiophen-4-yl)phenyl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane. A nitrogen flushed mixture of 4-(3- bromophenyl)dibenzo[6,<i]thiophene (2.4 g 7.07 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2-dioxaborolane (3.58 g, 14 mmol), Pd(dppf)Cl2 (114 mg, 0.14 mmol) and KOAc (2.08g, 21.2 mmol) was heated in dioxane (100 mL) at 90 0C for 18 h. After the mixture cooled to room temperature, ethyl acetate was added and the organic layer was washed with water, washed with brine, dried over anhydrous Na2SO4 and filtered. Celite was added to the filtrate and then concentrated by vacuum. The residue was purified by flash chromatography on silica (hexane: dichloromethane) followed by vacuum distillation (Kugelrohr) to remove the excess 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane and then crystallized from hexanes: ethyl acetate to give 2-(3-(dibenzo[δ,<i]thiophen-4-yl)phenyl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (1.62 g, 59%).
Figure imgf000064_0001
Compound 1
[0115] Step 7. Synthesis of 3-(3-(dibenzo [b,d] thiophen-4-yl)phenyl)dibenzo [f,h] iso- quinoline. The mixture of Step 4 product dibenzo[f,h]isoquinolin-3-yl trifluoromethanesulfonate (1.1 g, 2.9 mmol), Step 6 product 2-(3-(dibenzo[b,d]thiophen-4- yl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.5 g, 3.8 mmol), potassium phosphate tribasic monohydrate (2.0 g, 8.8 mmol), 150 mL toluene and 15 mL water was prepared and bubbled with nitrogen for 20 minutes. Then tris(dibenzylideneacetone)dipalladium(0) (27 mg, 0.029 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (48 mg, 0.12 mmol) were added to the mixture. The reaction mixture was bubbled with nitrogen for another 20 minutes and then refluxed overnight. After cooled to room temperature, 2-(3- (dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.3 g, 3.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.066 mmol) and 2- dicyclohexylphosphino-2',6'-dimethoxybiphenyl (100 mg, 0.24 mmol) were added to the mixture. The reaction mixture was bubbled with nitrogen for 30 minutes and then refluxed overnight. The mixture then was cooled to room temperature. The organic layer was collected and dried by MgSO4. The crude product was purified by silica gel column to give white solid Compound 1 (1.0 g, 71% yield).
Example 2. Synthesis of Compound 79
[0116] Synthesis of ligand 3-phenyldibenzo[f,h]isoquinoline. Dibenzo[f,h]isoquinolin-3- yl trifluoromethanesulfonate compound as synthesized in above Step 4 of Compound 1 synthesis reacts with phenylboronic acid under Suzuki reaction condition as described in Step 7 of Compound 1 synthesis to give the ligand 3-phenyldibenzo[f,h]isoquinoline.
Figure imgf000065_0001
Compound 79
[0117] Synthesis of Iridium complex Compound 79. 3-Phenyldibenzo[f,h]isoquinoline ligand mixed with Ir(acac)3 in ethylene glycol are heated up to reflux under nitrogen overnight to give Compound 79. The molar ratio of ligand and Ir(acac)3 is about 3.5 to 1.
Device Examples
[0118] All example devices were fabricated by high vacuum
Figure imgf000065_0002
Torr) thermal evaporation. The anode electrode is approximately 800 A or 1200 A of indium tin oxide (ITO). The cathode consisted of 10 A of LiF followed by 1000 A of Al. All devices are encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<lppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package.
[0119] Particular devices are provided wherein an invention compound, Compound 1, is the host material and the blocking layer material and El is the emitting dopant. The organic stack of Device Examples 1-4 consisted of sequentially, from the ITO surface, 100 A of El as the hole injecting layer (HIL), 300 A of 4,4'-bis-[N-(l-napthyl)-N-phenylamino]biphenyl (α- NPD) as the hole transport layer (HTL), 300 A of Compound 1 doped with 10-15 % of El, an Ir phosphorescent compound, as the emissive layer (EML), no blocking layer (0 A) or 50 A of Compound 1 as the blocking layer (BL) and 450 A or 500 A OfAIq3 (tris-8- hydroxyquinoline aluminum) as the electron transport layer (ETL).
[0120] Comparative Examples 1 and 2 were fabricated similarly to the Device Examples except that the CBP is used as the host and HPT was used as the BL material or there was no blocking layer.
[0121] As used herein, the following compounds have the following structures:
Figure imgf000066_0001
[0122] The device structures and device data are summarized below in Table 3 and Table 4. Table 3 shows the device structures and Table 4 shows the corresponding measured results for those devices.
[0123] The following terms are used in Tables 3 and 4, and are defined herein:
Comp. Ex. is an abbreviation for Comparative example. Ex. is an abbreviation for example. Cmpd. is an abbreviation for Compound. LE is luminous efficiency, which is defined as the luminance divided by the driving current density of the OLED. EQE is external quantum efficiency, which is defined as the ratio of measured number of photons to the electrons passed across the junction. PE is power efficiency, which is defined as the total luminous flux emitted divided by the total power input. Lo is the initial luminance, which is defined as the initial brightness at a certain current density. RTso% is a measure of lifetime, which is defined as the time required for the initial luminance, Lo, to decay to 80% of its value, at a constant current density of 40 mA/cm2 at room temperature.
TABLE 3
Figure imgf000066_0002
TABLE 4
Figure imgf000066_0003
Figure imgf000067_0001
[0124] The devices of Comparative Example 1 and Comparative Example 2 use thicknesses and dopant concentrations that were optimized for combinations of materials used in previous device studies. Device Example 1 and Device Example 2 have the same device structure and concentration of materials as used in Comparative Example 1 and Comparative Example 2, but the novel 2-azatriphenylene compounds provided herein have been substituted in place of CBP as the host material and HPT as the blocking layer material. It can be seen from these device examples that Compound 1 as a host in green phosphorescent OLEDs gives high device efficiency (LE>40 cd/A at 1000 cd/m2), indicating the azatriphenylenes linked with dibenzothiophenes, have triplet energy high enough for efficient green electrophosphorescence. This is consistent with the experimental results that the triplet energy of Compound 1 (Tl : 476 nm), which is high enough to accommodate a green phosphorescent dopant.
[0125] Device Example 2 and Comparative Example 2 results suggest that, as predicted, the Compound 1 host can significantly increase efficiency without a hole blocking layer because it is more electron transporting material as indicated by the relatively low LUMO of the 2-azatriphenylene moiety.
[0126] While demonstrating generally favorable properties of the novel 2-azatriphenylene compounds provided herein, Device Examples 1 and 2 were not optimized for lifetime analysis. In Device Example 3 and Device Example 4 the dopant concentration was adjusted as appropriate for these materials to measure device lifetime. In Device Examples 3 and 4, it can be seen that the 2-azatriphenylene compounds significantly improve lifetime, as compared to Comparative Example 1 and Comparative Example 2 respectively. In addition, the Device Examples 3 and 4 improve lifetime while maintaining good efficiency. [0127] The high stability of devices incorporating Compound 1 as the host is notable in Device Example 3 and 4. The lifetime, Tso% (defined as the time required for the initial luminance, Lo, to decay to 80% of its value, at a constant current density of 40 mA/cm2 at room temperature) for Device Example 3 and Comparative 1 are 136 hours and 105 hours respectively, with Device Example 1 having a slightly higher Lo.
[0128] The data suggest that hosts containing azatriphenylenes are good host and enhancement layer materials for phosphorescent OLEDs, providing as least the similar efficiency and improvement in stability compared to the commonly used CBP as the host. More conjugated versions of triphenylene containing benzoselenophenes, for example triphenylene and dibenzoselenophene units linked via/?-phenylene (such as 4,4'-biphenyl) may be very suitable for lower energy (yellow to red) phosphorescent OLEDs.
[0129] It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore includes variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

Claims

CLAIMS:
1. A compound including the structure:
Figure imgf000069_0001
FORMULA I, wherein R1, R2, and R3 may represent mono, di, tri, or tetra substitutions; wherein R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and wherein at least one OfR1, R2, and R3 is an aryl or heteroaryl.
2. The compound of claim 1, wherein the compound has the formula:
Figure imgf000069_0002
FORMULA I; and wherein the compound is not coordinated to a metal.
3. The compound of claim 1, wherein R3 is a substitution ortho to the nitrogen.
4. The compound of claim 1, wherein R1 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
5. The compound of claim 1, wherein R1 is an aryl or a heteroaryl.
6. The compound of claim 1, wherein R2 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
7. The compound of claim 1, wherein R2 is an aryl of heteroaryl.
8. The compound of claim 1, wherein R3 is selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
9. The compound of claim 1, wherein R3 is an aryl or heteroaryl.
10. The compound of claim 1, wherein each OfR1, R2, and R3 is an aryl or heteroaryl.
11. The compound of claim 1 , wherein the compound is selected from the
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000071_0002
Compound 9G
Figure imgf000071_0004
Figure imgf000071_0003
Compound 11 G Compound 12G
Figure imgf000071_0005
Figure imgf000072_0001
Compound 15G
Figure imgf000072_0002
Figure imgf000072_0003
Compound 17G Compound 18G
Figure imgf000072_0004
Compound 19G Compound 2OG
Figure imgf000072_0005
Figure imgf000073_0001
Compound 24G
Figure imgf000073_0002
Figure imgf000073_0003
Figure imgf000073_0004
Compound 28G
Figure imgf000073_0005
Figure imgf000073_0006
Figure imgf000074_0001
Compound 32G
Figure imgf000074_0002
Compound 33G
Figure imgf000074_0003
Figure imgf000074_0004
Compound 36G
Figure imgf000074_0005
Figure imgf000075_0001
Compound 4OG
Figure imgf000075_0002
Figure imgf000075_0003
Compound 44G
Figure imgf000075_0004
Figure imgf000075_0005
Compound 45G
Figure imgf000075_0006
Figure imgf000076_0002
Compound 47G
Figure imgf000076_0001
Compound 48G
Figure imgf000076_0003
Compound 49G
Figure imgf000076_0005
Compound 51 G
Figure imgf000076_0004
Compound 52G
Figure imgf000076_0006
Figure imgf000077_0001
Figure imgf000078_0001
Compound 64G
Compound 63G
Figure imgf000078_0002
Compound 66G
Figure imgf000078_0003
Compound 67G R4 Compound 68G
Figure imgf000078_0004
Compound 7OG
Compound 69G wherein R'3, R4, R5, R6, R7, and Rs may represent mono, di, tri, terra, or penta substitutions; and wherein R'3, R4, R5, R6, R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
12. The compound of claim 1, wherein R1, R2, R3, R4, R5, R6, R7, and Rs are hydrogen.
13. The compound of claim 1, wherein the compound comprises a ligand L having the formula:
Figure imgf000079_0001
FORMULA II, wherein A is a 5-membered or 6-membered aryl or heteroaryl ring; wherein RA may represent a mono, di, tri, or tetra substitution; wherein RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and wherein the ligand L is coordinated to a metal having an atomic number greater than 40.
14. The compound of claim 13, wherein the metal is Ir.
15. The compound of claim 14, wherein the ligand L is included in a homoleptic compound.
16. The compound of claim 14, wherein the ligand L is included in a heteroleptic compound.
17. The compound of claim 16, wherein the compound has the formula (L)n(L')3.nIr: wherein n is 1 or 2; wherein L' is selected from the group consisting of:
Figure imgf000080_0001
wherein K\ and R'2 may represent a mono, di, tri, or tetra substitution; wherein K\ and R'2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and wherein L has a different structure than L'.
18. The compound of claim 17, wherein n is 1.
19. The compound of claim 17, wherein n is 2.
20. The compound of claim 13, wherein the ligand L is selected from the group consisting of:
Figure imgf000080_0002
Figure imgf000080_0003
Compound 72G Compound 73G
Figure imgf000081_0001
Compound 76G Compound 77G Compound 78G wherein R4 and R5 may represent mono, di, tri, terra, or penta substitutions; and wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
21. The compound of claim 1 , wherein the ligand L is selected from the group consisting of:
Figure imgf000081_0002
Compound 71 Compound 72 Compound 73
Figure imgf000082_0001
Compound 74 Compound 75 Compound 75'
Figure imgf000082_0002
Compound 76 Compound 77 Compound 78
22. The compound of claim 1, wherein the compound is selected from the group consisting of:
Figure imgf000082_0003
Compound 79 Compound 80 Compound 81
Figure imgf000083_0001
Compound 83 Compound 84
Figure imgf000083_0002
Figure imgf000083_0003
Compound 85 Compound 86 Compound 87
Figure imgf000083_0004
Compound 88
Figure imgf000083_0005
Figure imgf000084_0001
Compound 90 Compound 91
Figure imgf000084_0002
Compound 92
Figure imgf000084_0003
Figure imgf000084_0004
Compound 94
Figure imgf000085_0001
Compound 95 Compound 96
23. The compound of claim 1, wherein the compound is selected from the group consisting of:
Figure imgf000085_0002
Compound 79 Compound 80 Compound 81
Figure imgf000085_0003
Compound 82 Compound 83 Compound 84
Figure imgf000086_0001
Compound 85 Compound 86 Compound 87
Figure imgf000086_0002
Compound 88 Compound 89 Compound 90
Figure imgf000086_0003
Compound 91 Compound 92 Compound 93
Figure imgf000087_0001
Compound 94 Compound 95
Figure imgf000087_0002
Compound 96
24. An organic light emitting device, comprising: an anode; a cathode; and a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound that includes the structure:
Figure imgf000087_0003
FORMULA I, wherein R1, R2, and R3 may represent mono, di, tri, or tetra substitutions; wherein R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and wherein at least one OfR1, R2, and R3 is an aryl or heteroaryl.
25. The device of claim 24, wherein the compound has the formula:
Figure imgf000088_0001
FORMULA I; and wherein the compound is not coordinated to a metal.
26. The device of claim 25, wherein the compound is selected from the group consisting of:
Figure imgf000088_0002
Figure imgf000089_0001
Figure imgf000089_0002
Compound 9G
Figure imgf000089_0004
Figure imgf000089_0003
Compound 11 G Compound 12G
Figure imgf000089_0005
Figure imgf000090_0001
Compound 15G
Figure imgf000090_0002
Figure imgf000090_0003
Compound 17G Compound 18G
Figure imgf000090_0004
Compound 19G Compound 2OG
Figure imgf000090_0005
Figure imgf000091_0001
Compound 24G
Figure imgf000091_0002
Figure imgf000091_0003
Figure imgf000091_0004
Compound 28G
Figure imgf000091_0005
Figure imgf000091_0006
Figure imgf000092_0001
Compound 32G
Figure imgf000092_0002
Compound 33G
Figure imgf000092_0003
Figure imgf000092_0004
Compound 36G
Figure imgf000092_0005
Figure imgf000093_0001
Compound 4OG
Figure imgf000093_0002
Figure imgf000093_0003
Compound 44G
Figure imgf000093_0004
Figure imgf000093_0005
Compound 45G
Figure imgf000093_0006
Figure imgf000094_0002
Compound 47G
Figure imgf000094_0001
Compound 48G
Figure imgf000094_0003
Compound 49G
Figure imgf000094_0005
Compound 51 G
Figure imgf000094_0004
Compound 52G
Figure imgf000094_0006
Figure imgf000095_0001
Figure imgf000096_0001
Compound 64G
Compound 63G
Figure imgf000096_0002
Compound 66G
Figure imgf000096_0003
Compound 67G R4 Compound 68G
Figure imgf000096_0004
Compound 7OG
Compound 69G wherein R'3, R4, R5, R6, R7, and Rs may represent mono, di, tri, terra, or penta substitutions; and wherein R'3, R4, R5, R6, R7, and Rs are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl.
27. The device of claim 24, wherein the first organic layer is an emissive layer and the compound including the structure FORMULA I is a host.
28. The device of claim 27, wherein the first organic layer further comprises an emitting dopant.
29. The device of claim 28, wherein the emitting dopant has the formula:
Figure imgf000097_0001
E1 wherein Rx and Ry may represent mono, di, tri, or tetra substitutions; and wherein Rx and Ry are independently selected from the group consisting of hydrogen, alkyl, and aryl.
30. The device of claim 24, wherein the compound comprises a ligand L having the formula:
Figure imgf000097_0002
FORMULA II, wherein A is a 5-membered or 6-membered aryl or heteroaryl ring; wherein RA may represent a mono, di, tri, or tetra substitution; wherein RA is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, and heteroaryl; and wherein the ligand L is coordinated to a metal having an atomic number greater than 40.
31. The device of claim 30, wherein the ligand L is selected from the group consisting of:
Figure imgf000098_0001
Compound 74G Compound 75G
Figure imgf000099_0001
Compound 76G Compound 77G Compound 78G wherein R4 and R5 may represent mono, di, tri, tetra, or penta substitutions; and wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl.
32. The device of claim 30, wherein the compound is selected from the group consisting of:
Figure imgf000099_0002
Compound 79 Compound 80 Compound 81
Figure imgf000100_0001
Compound 83 Compound 84
Figure imgf000100_0002
Figure imgf000100_0003
Compound 85 Compound 86 Compound 87
Figure imgf000100_0004
Compound 88
Figure imgf000100_0005
Figure imgf000101_0001
Compound 90 Compound 91
Figure imgf000101_0002
Compound 92
Figure imgf000101_0003
Figure imgf000101_0004
Compound 94
Figure imgf000102_0001
Compound 95 Compound 96
33. The device of claim 30, wherein the first organic layer is an emissive layer and the compound including the structure FORMULA II is an emitting dopant.
34. The device of claim 33, wherein the first organic layer further comprises a host material.
35. The device of claim 24, wherein the device has a second organic layer that is a non-emissive layer and the compound including the structure FORMULA II is a non- emissive material in the second organic layer.
36. The device of claim 35, wherein the second organic layer is a hole injection or transport layer and the compound including the structure FORMULA II is a hole injection or transport material in the second organic layer.
37. A consumer product comprising a device, the device further comprising: an anode; a cathode; and a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound that includes the structure:
Figure imgf000102_0002
FORMULA I, wherein R1, R2, and R3 may represent mono, di, tri, or tetra substitutions; wherein R1, R2, and R3 are independently selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl, heteroaryl and hydrogen; and wherein at least one OfR1, R2, and R3 is an aryl or heteroaryl.
PCT/US2010/034479 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes WO2010132524A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN2010800280229A CN102482222A (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes
KR1020117029712A KR101738534B1 (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes
EP10720077.6A EP2429997B1 (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes
JP2012510966A JP5937002B2 (en) 2009-05-12 2010-05-12 2-Azatriphenylene materials for organic light-emitting diodes
KR1020177013084A KR101884581B1 (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US17743509P 2009-05-12 2009-05-12
US61/177,435 2009-05-12
US12/778,362 US9005771B2 (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes
US12/778,362 2010-05-12

Publications (1)

Publication Number Publication Date
WO2010132524A1 true WO2010132524A1 (en) 2010-11-18

Family

ID=42246255

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/034479 WO2010132524A1 (en) 2009-05-12 2010-05-12 2-azatriphenylene materials for organic light emitting diodes

Country Status (7)

Country Link
US (1) US9005771B2 (en)
EP (2) EP2520571B1 (en)
JP (2) JP5937002B2 (en)
KR (2) KR101738534B1 (en)
CN (2) CN107325089B (en)
TW (1) TWI541234B (en)
WO (1) WO2010132524A1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013010742A (en) * 2011-06-29 2013-01-17 Samsung Display Co Ltd New heterocyclic compound and organic light-emitting element including the same
JP2013035825A (en) * 2011-07-08 2013-02-21 Semiconductor Energy Lab Co Ltd Heterocyclic compound, light-emitting element, light-emitting device, electronic equipment and lighting apparatus
JP2013060413A (en) * 2011-02-01 2013-04-04 Semiconductor Energy Lab Co Ltd Heterocyclic compound
JP2013118368A (en) * 2011-11-04 2013-06-13 Semiconductor Energy Lab Co Ltd Dibenzo[f,h]quinoxaline compound, light-emitting element, light-emitting device, electronic device, and lighting device
JP2014029973A (en) * 2011-08-31 2014-02-13 Semiconductor Energy Lab Co Ltd Light-emitting element, light-emitting device, electronic device, luminaire, and heterocyclic compound
JP2014504602A (en) * 2011-01-24 2014-02-24 ユニバーサル ディスプレイ コーポレイション Electron transport compounds
WO2014112450A1 (en) * 2013-01-17 2014-07-24 Canon Kabushiki Kaisha Organic light-emitting element
JP2015078228A (en) * 2010-03-01 2015-04-23 株式会社半導体エネルギー研究所 Compound
WO2015139808A1 (en) 2014-03-18 2015-09-24 Merck Patent Gmbh Organic electroluminescent device
JP2016184743A (en) * 2011-02-01 2016-10-20 株式会社半導体エネルギー研究所 Light-emitting element with heterocyclic compound, light-emitting device, electronic apparatus, and illumination device

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5305637B2 (en) 2007-11-08 2013-10-02 キヤノン株式会社 Organometallic complex, organic light emitting device using the same, and display device
JP5604848B2 (en) * 2009-10-19 2014-10-15 コニカミノルタ株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, LIGHTING DEVICE AND DISPLAY DEVICE
DE102010048608A1 (en) * 2010-10-15 2012-04-19 Merck Patent Gmbh Materials for organic electroluminescent devices
CN102127015B (en) * 2011-01-13 2013-06-19 北京交通大学 Perylene ring bridged benzophenanthrene compound and preparation method thereof
JP2013063963A (en) 2011-08-31 2013-04-11 Semiconductor Energy Lab Co Ltd Heterocyclic compound, light-emitting element, light-emitting element, electronic device and lighting device
US8766531B1 (en) * 2012-12-14 2014-07-01 Universal Display Corporation Wearable display
JP5818870B2 (en) * 2012-12-27 2015-11-18 キヤノン株式会社 Organic light emitting device and display device
JP6253971B2 (en) * 2012-12-28 2017-12-27 株式会社半導体エネルギー研究所 LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE
JP5984689B2 (en) 2013-01-21 2016-09-06 キヤノン株式会社 Organometallic complex and organic light emitting device using the same
JP6222931B2 (en) * 2013-01-21 2017-11-01 キヤノン株式会社 Organic light emitting device
KR102162793B1 (en) 2013-03-05 2020-10-08 삼성디스플레이 주식회사 Compound and organic light emitting device comprising the same
US9537106B2 (en) * 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
KR102188028B1 (en) 2013-06-18 2020-12-08 삼성디스플레이 주식회사 Organic light emitting device
JP6386299B2 (en) 2013-08-30 2018-09-05 株式会社半導体エネルギー研究所 Organic compounds for light emitting devices
KR102167048B1 (en) * 2013-12-03 2020-10-19 삼성디스플레이 주식회사 Compound and organic light emitting device comprising same
US9755159B2 (en) * 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
JP6780925B2 (en) 2014-07-25 2020-11-04 株式会社半導体エネルギー研究所 Light emitting elements, light emitting devices, electronic devices and lighting devices
CN105399749B (en) * 2015-10-21 2017-10-10 中节能万润股份有限公司 A kind of new OLED electron transport materials and its application
CN108137633A (en) * 2015-12-04 2018-06-08 广州华睿光电材料有限公司 Metal organic complex, high polymer, mixture, composition and organic electronic device
US12082500B2 (en) 2015-12-21 2024-09-03 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
KR102008895B1 (en) * 2016-05-31 2019-08-08 삼성에스디아이 주식회사 Organic compound for optoelectric device and organic optoelectric device and display device
KR102138823B1 (en) * 2017-12-27 2020-07-28 삼성에스디아이 주식회사 Organic optoelectric device and display device
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
KR20200115240A (en) * 2019-03-29 2020-10-07 삼성전자주식회사 Organometallic compound, organic light emitting device including the same and electronic device including the organic light emitting apparatus
CN112250667B (en) * 2019-07-22 2024-03-08 固安鼎材科技有限公司 Organic compound, application thereof and organic electroluminescent device using same
CN110698517B (en) * 2019-09-27 2022-05-20 吉林奥来德光电材料股份有限公司 Iridium metal complex, preparation method thereof and organic electroluminescent device
CN112592371A (en) * 2019-10-02 2021-04-02 环球展览公司 Organic electroluminescent material and device
US20210101921A1 (en) * 2019-10-02 2021-04-08 Universal Display Corporation Organic electroluminescent materials and devices
CN110759950B (en) * 2019-10-31 2022-03-15 吉林奥来德光电材料股份有限公司 Organic phosphorus luminescent material, preparation method thereof and organic electroluminescent device prepared from organic phosphorus luminescent material
KR20210079766A (en) * 2019-12-20 2021-06-30 삼성전자주식회사 Organometallic compound and organic light emitting device including the same
CN111825723A (en) * 2020-07-15 2020-10-27 奥来德(上海)光电材料科技有限公司 Organic iridium metal complex and preparation method and application thereof
CN111690019A (en) * 2020-07-15 2020-09-22 奥来德(上海)光电材料科技有限公司 Organic iridium metal complex and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1555269A1 (en) * 2004-01-13 2005-07-20 LG Electronics Inc. Phenyl pyridine-iridium metal complex compounds for organic electroluminescent device, process for preparing the compounds, and organic electroluminescent device using the compounds
WO2009021126A2 (en) * 2007-08-08 2009-02-12 Universal Display Corporation Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group
WO2009060995A1 (en) * 2007-11-08 2009-05-14 Canon Kabushiki Kaisha Organic metal complex, and organic light emitting device and display apparatus using the same
EP2103665A1 (en) * 2008-03-19 2009-09-23 Gracel Display Inc. Novel organic electroluminescent compounds and organic electroluminescent device using the same

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4769292A (en) * 1987-03-02 1988-09-06 Eastman Kodak Company Electroluminescent device with modified thin film luminescent zone
GB8909011D0 (en) * 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
US5061569A (en) * 1990-07-26 1991-10-29 Eastman Kodak Company Electroluminescent device with organic electroluminescent medium
EP0650955B1 (en) 1993-11-01 1998-08-19 Hodogaya Chemical Co., Ltd. Amine compound and electro-luminescence device comprising same
US5703436A (en) * 1994-12-13 1997-12-30 The Trustees Of Princeton University Transparent contacts for organic devices
US5707745A (en) 1994-12-13 1998-01-13 The Trustees Of Princeton University Multicolor organic light emitting devices
AU681934B2 (en) * 1995-03-14 1997-09-11 Kalford Pty Ltd A hinge
US5844363A (en) 1997-01-23 1998-12-01 The Trustees Of Princeton Univ. Vacuum deposited, non-polymeric flexible organic light emitting devices
US6091195A (en) * 1997-02-03 2000-07-18 The Trustees Of Princeton University Displays having mesa pixel configuration
US5834893A (en) * 1996-12-23 1998-11-10 The Trustees Of Princeton University High efficiency organic light emitting devices with light directing structures
US6013982A (en) * 1996-12-23 2000-01-11 The Trustees Of Princeton University Multicolor display devices
US6303238B1 (en) 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
US6337102B1 (en) 1997-11-17 2002-01-08 The Trustees Of Princeton University Low pressure vapor phase deposition of organic thin films
US6087196A (en) * 1998-01-30 2000-07-11 The Trustees Of Princeton University Fabrication of organic semiconductor devices using ink jet printing
US6830828B2 (en) * 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6097147A (en) * 1998-09-14 2000-08-01 The Trustees Of Princeton University Structure for high efficiency electroluminescent device
US6294398B1 (en) * 1999-11-23 2001-09-25 The Trustees Of Princeton University Method for patterning devices
US6458475B1 (en) 1999-11-24 2002-10-01 The Trustee Of Princeton University Organic light emitting diode having a blue phosphorescent molecule as an emitter
US20020121638A1 (en) 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
JP3812730B2 (en) * 2001-02-01 2006-08-23 富士写真フイルム株式会社 Transition metal complex and light emitting device
US7071615B2 (en) 2001-08-20 2006-07-04 Universal Display Corporation Transparent electrodes
US7431968B1 (en) * 2001-09-04 2008-10-07 The Trustees Of Princeton University Process and apparatus for organic vapor jet deposition
US6835469B2 (en) * 2001-10-17 2004-12-28 The University Of Southern California Phosphorescent compounds and devices comprising the same
US7166368B2 (en) 2001-11-07 2007-01-23 E. I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
US6863997B2 (en) * 2001-12-28 2005-03-08 The Trustees Of Princeton University White light emitting OLEDs from combined monomer and aggregate emission
KR100691543B1 (en) 2002-01-18 2007-03-09 주식회사 엘지화학 New material for transporting electron and organic electroluminescent display using the same
US20030230980A1 (en) * 2002-06-18 2003-12-18 Forrest Stephen R Very low voltage, high efficiency phosphorescent oled in a p-i-n structure
US6687266B1 (en) * 2002-11-08 2004-02-03 Universal Display Corporation Organic light emitting materials and devices
WO2004093207A2 (en) 2003-04-15 2004-10-28 Covion Organic Semiconductors Gmbh Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
US7029765B2 (en) * 2003-04-22 2006-04-18 Universal Display Corporation Organic light emitting devices having reduced pixel shrinkage
CN100483779C (en) 2003-05-29 2009-04-29 新日铁化学株式会社 Organic electroluminescent element
JP2005011610A (en) 2003-06-18 2005-01-13 Nippon Steel Chem Co Ltd Organic electroluminescent element
US20050025993A1 (en) * 2003-07-25 2005-02-03 Thompson Mark E. Materials and structures for enhancing the performance of organic light emitting devices
TWI390006B (en) 2003-08-07 2013-03-21 Nippon Steel Chemical Co Organic EL materials with aluminum clamps
US20060269780A1 (en) 2003-09-25 2006-11-30 Takayuki Fukumatsu Organic electroluminescent device
TW200531592A (en) 2004-03-15 2005-09-16 Nippon Steel Chemical Co Organic electroluminescent device
US7491823B2 (en) * 2004-05-18 2009-02-17 The University Of Southern California Luminescent compounds with carbene ligands
US7279704B2 (en) * 2004-05-18 2007-10-09 The University Of Southern California Complexes with tridentate ligands
JP4894513B2 (en) 2004-06-17 2012-03-14 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
US20060008670A1 (en) * 2004-07-06 2006-01-12 Chun Lin Organic light emitting materials and devices
EP2271183B1 (en) 2004-07-23 2015-03-18 Konica Minolta Holdings, Inc. Organic electroluminescent element, display and illuminator
DE102004057072A1 (en) 2004-11-25 2006-06-01 Basf Ag Use of Transition Metal Carbene Complexes in Organic Light Emitting Diodes (OLEDs)
GB2437453B (en) 2005-02-04 2011-05-04 Konica Minolta Holdings Inc Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device
KR100803125B1 (en) * 2005-03-08 2008-02-14 엘지전자 주식회사 Red phosphorescent compounds and organic electroluminescence devices using the same
WO2006098120A1 (en) 2005-03-16 2006-09-21 Konica Minolta Holdings, Inc. Organic electroluminescent device material and organic electroluminescent device
JPWO2006103874A1 (en) 2005-03-29 2008-09-04 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
US8231983B2 (en) 2005-04-18 2012-07-31 Konica Minolta Holdings Inc. Organic electroluminescent device, display and illuminating device
US9051344B2 (en) * 2005-05-06 2015-06-09 Universal Display Corporation Stability OLED materials and devices
EP2277978B1 (en) 2005-05-31 2016-03-30 Universal Display Corporation Triphenylene hosts in phosphorescent light emitting diodes
JP4976288B2 (en) 2005-06-07 2012-07-18 新日鐵化学株式会社 Organometallic complex and organic electroluminescence device using the same
WO2007004380A1 (en) 2005-07-01 2007-01-11 Konica Minolta Holdings, Inc. Organic electroluminescent element material, organic electroluminescent element, display device, and lighting equipment
JP4887731B2 (en) 2005-10-26 2012-02-29 コニカミノルタホールディングス株式会社 Organic electroluminescence element, display device and lighting device
CN102633820B (en) 2005-12-01 2015-01-21 新日铁住金化学株式会社 Compound for organic electroluminescent element and organic electroluminescent element
US20090295276A1 (en) 2005-12-01 2009-12-03 Tohru Asari Organic Electroluminescent Device
JP4972938B2 (en) 2006-01-12 2012-07-11 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
EP2399922B1 (en) * 2006-02-10 2019-06-26 Universal Display Corporation Metal complexes of cyclometallated imidazo(1,2-f) phenanthridine and diimidazo(1,2-A;1',2'-C)quinazoline ligands and isoelectronic and benzannulated analogs therof
JP4823730B2 (en) 2006-03-20 2011-11-24 新日鐵化学株式会社 Luminescent layer compound and organic electroluminescent device
CN104835914B (en) * 2006-12-28 2018-02-09 通用显示公司 Long lifetime phosphorescent organic light emitting device part (OLED) structure
ATE522588T1 (en) * 2007-04-04 2011-09-15 Basf Se IRIDIUM-TRIPHENYLENE COMPLEXES AND THEIR USE IN OLEDS
KR20090010883A (en) * 2007-07-23 2009-01-30 소니 가부시끼가이샤 Organic electroluminescent device and display device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1555269A1 (en) * 2004-01-13 2005-07-20 LG Electronics Inc. Phenyl pyridine-iridium metal complex compounds for organic electroluminescent device, process for preparing the compounds, and organic electroluminescent device using the compounds
WO2009021126A2 (en) * 2007-08-08 2009-02-12 Universal Display Corporation Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group
WO2009060995A1 (en) * 2007-11-08 2009-05-14 Canon Kabushiki Kaisha Organic metal complex, and organic light emitting device and display apparatus using the same
EP2103665A1 (en) * 2008-03-19 2009-09-23 Gracel Display Inc. Novel organic electroluminescent compounds and organic electroluminescent device using the same

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BALDO ET AL.: "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices", NATURE, vol. 395, 1998, pages 151 - 154, XP001002103, DOI: doi:10.1038/25954
BALDO ET AL.: "Very high-efficiency green organic light-emitting devices based on electrophosphorescence", APPL. PHYS. LETT., vol. 75, no. 3, 1999, pages 4 - 6, XP012023409, DOI: doi:10.1063/1.124258
HEWLINE, M. ET AL., SYNTHESIS, vol. 14, 2007, pages 2157 - 2163
MCIVER A ET AL: "A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine", CHEMICAL COMMUNICATIONS, no. 39, 21 October 2008 (2008-10-21), pages 4750 - 4652, XP009135250, ISSN: 1359-7345, DOI: 10.1039/b811068a *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10224490B2 (en) 2010-03-01 2019-03-05 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US9899608B2 (en) 2010-03-01 2018-02-20 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
JP2015078228A (en) * 2010-03-01 2015-04-23 株式会社半導体エネルギー研究所 Compound
KR101923238B1 (en) * 2011-01-24 2018-11-28 유니버셜 디스플레이 코포레이션 Aza - dibenzothiophene, aza - dibenzofuran and aza - dibenzoselenophene derivatives for use in oled's
JP2014504602A (en) * 2011-01-24 2014-02-24 ユニバーサル ディスプレイ コーポレイション Electron transport compounds
JP2016199564A (en) * 2011-01-24 2016-12-01 ユニバーサル ディスプレイ コーポレイション Electron transporting compounds
JP2016184743A (en) * 2011-02-01 2016-10-20 株式会社半導体エネルギー研究所 Light-emitting element with heterocyclic compound, light-emitting device, electronic apparatus, and illumination device
JP2013060413A (en) * 2011-02-01 2013-04-04 Semiconductor Energy Lab Co Ltd Heterocyclic compound
KR101861750B1 (en) 2011-02-01 2018-05-28 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Heterocycle compound
US9960368B2 (en) 2011-02-01 2018-05-01 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound
JP2013010742A (en) * 2011-06-29 2013-01-17 Samsung Display Co Ltd New heterocyclic compound and organic light-emitting element including the same
US9309223B2 (en) 2011-07-08 2016-04-12 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US9843000B2 (en) 2011-07-08 2017-12-12 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
JP2013035825A (en) * 2011-07-08 2013-02-21 Semiconductor Energy Lab Co Ltd Heterocyclic compound, light-emitting element, light-emitting device, electronic equipment and lighting apparatus
JP2014029973A (en) * 2011-08-31 2014-02-13 Semiconductor Energy Lab Co Ltd Light-emitting element, light-emitting device, electronic device, luminaire, and heterocyclic compound
JP2017139474A (en) * 2011-11-04 2017-08-10 株式会社半導体エネルギー研究所 Light-emitting element, light-emitting device, electronic device, and lighting device
JP2013118368A (en) * 2011-11-04 2013-06-13 Semiconductor Energy Lab Co Ltd Dibenzo[f,h]quinoxaline compound, light-emitting element, light-emitting device, electronic device, and lighting device
US9466804B2 (en) 2013-01-17 2016-10-11 Canon Kabushiki Kaisha Organic light-emitting element
JP2014138100A (en) * 2013-01-17 2014-07-28 Canon Inc Organic light-emitting element
WO2014112450A1 (en) * 2013-01-17 2014-07-24 Canon Kabushiki Kaisha Organic light-emitting element
WO2015139808A1 (en) 2014-03-18 2015-09-24 Merck Patent Gmbh Organic electroluminescent device

Also Published As

Publication number Publication date
EP2429997B1 (en) 2014-01-15
US20100289406A1 (en) 2010-11-18
KR101738534B1 (en) 2017-05-23
TWI541234B (en) 2016-07-11
EP2520571A1 (en) 2012-11-07
KR20120023780A (en) 2012-03-13
CN107325089A (en) 2017-11-07
KR20170056035A (en) 2017-05-22
CN107325089B (en) 2021-07-13
EP2429997A1 (en) 2012-03-21
JP2016104745A (en) 2016-06-09
JP5937002B2 (en) 2016-06-22
JP6025959B2 (en) 2016-11-16
EP2520571B1 (en) 2016-08-17
JP2012526833A (en) 2012-11-01
CN102482222A (en) 2012-05-30
TW201111347A (en) 2011-04-01
US9005771B2 (en) 2015-04-14
KR101884581B1 (en) 2018-08-01

Similar Documents

Publication Publication Date Title
KR102133124B1 (en) Novel heteroleptic iridium complexes
JP6025959B2 (en) 2-Azatriphenylene materials for organic light-emitting diodes
KR102118826B1 (en) Cyclometallated tetradentate pt(ii) complexes comprised of one or two imidazole rings with a twisted aryl group bonded to n-1
JP6431949B2 (en) Heteroleptic iridium carbene complex and light emitting device using the same
JP6316351B2 (en) Pyridylcarbene phosphor photoluminescent material
JP5981603B2 (en) Heteroleptic iridium complex
JP6076949B2 (en) New materials with aza-dibenzothiophene or aza-dibenzofuran nuclei for PHOLED
JP2017014275A (en) Novel organic light emitting materials
EP3081617A1 (en) Blue emitter with high efficiency based on imidazo [1,2-f] phenanthridine iridium complexes
WO2009085344A2 (en) Dibenzothiophene-containing materials in phosphorescent light emitting diodes

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201080028022.9

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10720077

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2012510966

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 9557/DELNP/2011

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2010720077

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 20117029712

Country of ref document: KR

Kind code of ref document: A